5'-O-三苯甲基-2',3'-去氢胸苷 | 5964-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 5'-O-三苯甲基-2',3'-去氢胸苷
• 英文名称: 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine
• 英文别名: 2',3'-didehydro-2',3'-dideoxy-5-methyl-5'-O-(triphenylmethyl)uridine；5'-O-Trityl-2',3'-dehydrothymidine；5-methyl-1-[(2R,5S)-5-(trityloxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
• CAS: 5964-41-0
• 化学式: C₂₉H₂₆N₂O₄
• 分子量: 466.536
• InChiKey: MIAKIEAKHPFXJJ-IZZNHLLZSA-N

物化性质

• 熔点：
  107-111 °C
• 密度：
  1.240±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-O-三苯甲基-2',3'-去氢胸苷 在 溶剂黄146 作用下， 生成 司他夫定
  参考文献：
  名称：

  一种新的不饱和无环核苷类似物的方法和通过闭环复分解法首次合成d4T

  摘要：

  新型不饱和无环核苷类似物，1- {1- [1-（羟甲基）丙-2-烯氧基]丙-2-烯基}尿嘧啶，1- {1- [1- [1-（羟甲基）丙-2-烯氧基]丙-通过尿酸和5-甲基尿苷的高碘酸盐裂解，再加两次Wittig，从尿苷和5-甲基尿苷中以高收率制备了2-烯基胸腺嘧啶和1- {1- [1-（羟甲基）丙-2-烯氧基]丙-2-烯基}胞嘧啶引入两个乙烯基的反应。胸腺嘧啶衍生物进行了闭环复分解反应，以合成d4T。

  DOI：

  10.1016/s0040-4039(02)00572-5
• 作为产物：
  描述：

  5’-三苯甲基-2’-脱氧-2,3’-双脱氢胸苷 在 lithium aluminium tetrahydride 、 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 5'-O-三苯甲基-2',3'-去氢胸苷
  参考文献：
  名称：

  Selenium nucleophiles for the preparation of antiviral nucleosides

  摘要：

  The reactivity of nucleophilic selenium species toward nucleoside derivatives has been examined. A number of new 2'-deoxyribose nucleosides have been synthesized using this methodology. The cis elimination of the selenoxide obtained from the oxidation of the corresponding phenylselenide has been shown to be an efficient method for the preparation of the 2',3'-unsaturated antiviral nucleoside 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine (DAT).

  DOI：

  10.1021/jo00006a037

文献信息

• Synthesis of 2‘,3‘-Didehydro-2‘,3‘-dideoxynucleosides by Reaction of 5‘-Protected Nucleoside 2‘,3‘-Dimesylates with Telluride Dianion:  A General Route from <i>Cis</i> Vicinal Diols to Olefins
  作者：Derrick L. J. Clive、Philip L. Wickens、Paulo W. M. Sgarbi

  DOI：10.1021/jo9610570

  日期：1996.1.1

  treatment with telluride dianion in the form of the sodium or lithium salt. The method is well-suited to the preparation of unsaturated nucleosides that can be converted into compounds that are believed to be useful in the treatment of AIDS. The deoxygenation is general for vicinal dimesylates that have, or may adopt, a synperiplanar conformation. With straight chain compounds the reaction is stereospecific

  通过用钠或锂盐形式的碲化物二价阴离子处理，将5'-保护的核苷的2'，3'-二甲磺酸酯转化为相应的2'，3'-二氢-2'，3'-二脱氧化合物。该方法非常适合于不饱和核苷的制备，该不饱和核苷可以转化为据信可用于治疗艾滋病的化合物。脱氧通常用于具有或可以采用间平面构象的邻近二甲基酯。对于直链化合物，反应是立体特异性的。在某些情况下，可以用硒化物二价阴离子进行类似但较慢的脱氧。
• Simple Entry to 3‘-Substituted Analogues of Anti-HIV Agent Stavudine Based on an Anionic O → C Stannyl Migration
  作者：Hiroki Kumamoto、Hiromichi Tanaka

  DOI：10.1021/jo0107958

  日期：2002.5.1

  hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating

  研究了抗HIV药物司他夫定（d4T）的5'-O保护衍生物与LTMP的反应，目的是锂化乙烯基氢（H-3'和H-2'）。当5′-O-叔丁基二苯基甲硅烷基衍生物5的锂化在HMPA存在下进行时，发生阴离子甲硅烷基迁移，得到3′-C-甲硅烷基化产物4a。发现该反应的亚锡烷基形式也是可能的，其已经公开了通过操纵3'-C-锡烷基d4T作为共同中间体而非常简单地进入在3'-位被各种取代的d4T类似物。
• Reaction of cis-vicinal dimethanesulfonates with Te^2–: a method for converting cis-vicinal diols into olefins and its use in the preparation of 2′,3′-didehydro-2′,3′-dideoxynucleosides
  作者：Derrick L. J. Clive、Philip L. Wickens

  DOI：10.1039/c39930000923

  日期：——

  cis-Vicinal dimethanesulfonates, prepared from the corresponding diols, are converted into olefins by treatment with alkali metal tellurides or selenides (M2Te or M2Se); the reaction has been used to make derivatives of 2′,3′-didehydro-2′,3′-dideoxynucleosides.

  由相应二醇制备的顺式邻二甲磺酸酯，通过与碱金属碲化物或硒化物（M2Te或M2Se）处理，可转化为烯烃；该反应已被用于制备2′,3′-二脱氢-2′,3′-二脱氧核苷的衍生物。
• Synthesis of 2,2′-Anhydro-1-(3′-deoxy-3′-bromo-β-D-arabinofuranosyl)thymine and Its Derivatives from 5′-<i>O</i>-Trityl-2′,3′-thymidinene
  作者：Katsumaro Minamoto、Masataka Oishi、Akikazu Kakehi、Kenji Watanabe、Toyohide Takeuchi

  DOI：10.1246/cl.1992.2149

  日期：1992.11

  Reaction of 5′-O-trityl-2′,3′-thymidinene with hypobromous acid gave 2,2′-anhydro-1-(3′-deoxy-3′-bromo-5′-O-trityl-β-D-arabinofuranosyl)-(5R,6R)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine (3) and its (5S,6S) trans analogue (4). These were transformed into the corresponding 5,6-epoxy analogues. Compounds 3 and 4 were debromohydrinated to the title 2,2′-anhydro nucleoside in high yields.

  5'-O-trityl-2',3'-thymidinene 与次溴酸反应得到 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D -arabinofuranosyl)-(5R,6R)-trans-5-bromo-6-hydroxy-5,6-dihydrothymine (3) 及其 (5S,6S) 反式类似物 (4)。这些被转化为相应的 5,6-环氧类似物。化合物 3 和 4 以高产率脱溴氢化为标题 2,2'-脱水核苷。
• Synthesis of acyclic bis-vinyl pyrimidines: a general route to d4T via metathesis
  作者：D.F Ewing、V Glaçon、G Mackenzie、D Postel、C Len

  DOI：10.1016/s0040-4020(02)01661-7

  日期：2003.2

  Unsaturated acyclic pyrimidine analogues, 1-1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}uracil, 1-1-[1-(hydroxy-methyl)prop-2-enyloxy]prop-2-enyl}thymine and 1-1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}cytosine having two asymmetric carbon atoms have been prepared in good yield starting from uridine and 5-methyluridine. The bis-vinyl thymine derivative underwent ring closure metathesis to give d4T, thus providing a novel synthesis of this compound. (C) 2003 Elsevier Science Ltd. All rights reserved.